EP1535969A3 - Nouveaux colorants polymethine à base de coumarine avec Stoke's-Shift réglable - Google Patents
Nouveaux colorants polymethine à base de coumarine avec Stoke's-Shift réglable Download PDFInfo
- Publication number
- EP1535969A3 EP1535969A3 EP04028161A EP04028161A EP1535969A3 EP 1535969 A3 EP1535969 A3 EP 1535969A3 EP 04028161 A EP04028161 A EP 04028161A EP 04028161 A EP04028161 A EP 04028161A EP 1535969 A3 EP1535969 A3 EP 1535969A3
- Authority
- EP
- European Patent Office
- Prior art keywords
- hetero
- iii
- aliphatic
- ester
- polymethine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title 2
- 229960000956 coumarin Drugs 0.000 title 1
- 235000001671 coumarin Nutrition 0.000 title 1
- 239000000975 dye Substances 0.000 title 1
- 125000005842 heteroatom Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 imide ester Chemical class 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- DHQPQGBAUAMAEK-UHFFFAOYSA-N 4,6-dibromotriazine Chemical compound BrC1=CC(Br)=NN=N1 DHQPQGBAUAMAEK-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000858 Cyclodextrin Polymers 0.000 abstract 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 150000002463 imidates Chemical class 0.000 abstract 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 102000039446 nucleic acids Human genes 0.000 abstract 1
- 108020004707 nucleic acids Proteins 0.000 abstract 1
- 150000007523 nucleic acids Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 abstract 1
- 150000008300 phosphoramidites Chemical class 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003461 sulfonyl halides Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 229910052714 tellurium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Color Printing (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10356130 | 2003-11-26 | ||
DE10356130A DE10356130A1 (de) | 2003-11-28 | 2003-11-28 | Neue Polymethinfarbstoffe auf Cumarin-Basis mit einstellbarem Stokes-Shift |
Publications (3)
Publication Number | Publication Date |
---|---|
EP1535969A2 EP1535969A2 (fr) | 2005-06-01 |
EP1535969A3 true EP1535969A3 (fr) | 2005-06-08 |
EP1535969B1 EP1535969B1 (fr) | 2011-06-15 |
Family
ID=34485242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04028161A Active EP1535969B1 (fr) | 2003-11-28 | 2004-11-26 | Nouveaux colorants polymethine à base de coumarine avec Stoke's-Shift réglable |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1535969B1 (fr) |
AT (1) | ATE513015T1 (fr) |
DE (1) | DE10356130A1 (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005004745A1 (de) * | 2005-01-31 | 2006-08-10 | Dyomics Gmbh | Verfahren zu Nachweis und Quantifizierung von Proteinen |
WO2008013543A1 (fr) * | 2006-07-28 | 2008-01-31 | Pierce Biotechnology, Inc. | Composés de sondes à protéines, compositions et procédés |
US7553869B2 (en) | 2006-07-28 | 2009-06-30 | Pierce Biotechnology, Inc. | Protein probe compounds, compositions, and methods |
WO2008147805A2 (fr) * | 2007-05-22 | 2008-12-04 | Becton, Dickinson And Company | Teintes ayant une réponse de fluorescence ratiométrique pour détecter des métabolites |
US9097667B2 (en) | 2007-12-14 | 2015-08-04 | Biotium, Inc. | Fluorescent compounds |
US8658434B2 (en) | 2009-10-28 | 2014-02-25 | Biotium, Inc. | Fluorescent pyrene compounds |
DE102013114848A1 (de) | 2013-12-23 | 2015-08-13 | Dyomics Gmbh | Markerfarbstoffe für UV- und kurzwellige Anregung mit hohem Stokes Shift auf der Basis von Benzoxazolen |
CN104860915B (zh) * | 2015-04-10 | 2016-11-23 | 昆明理工大学 | 一种4h-4-芳基苯并吡喃类化合物的制备方法 |
ITUA20161706A1 (it) * | 2016-03-15 | 2017-09-15 | Cyanagen S R L | Nuovi coloranti cumarinici e relativi coniugati |
WO2018114710A1 (fr) | 2016-12-22 | 2018-06-28 | Illumina Cambridge Limited | Composés coumarines et leurs utilisations en tant que marqueurs fluorescents |
CN108558839B (zh) * | 2018-05-15 | 2021-03-23 | 三峡大学 | 一种香豆素-吡啶化合物,制备方法及其应用 |
WO2020178165A1 (fr) | 2019-03-01 | 2020-09-10 | Illumina Cambridge Limited | Composés de coumarine substitués par une amine tertiaire et leurs utilisations en tant que marqueurs fluorescents |
DE102020109362A1 (de) | 2020-04-03 | 2021-10-07 | Dyomics Gmbh | Fluoreszenzfarbstoffe mit hohem Stokes Shift auf der Basis von verbrückten Benzopyryliumsalzen |
CN114507223B (zh) * | 2022-02-28 | 2023-04-25 | 吕梁学院 | 一种吲哚盐-香豆素衍生物及其制备方法和应用、比率检测亚硫酸根的方法 |
Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945033A (en) * | 1957-05-29 | 1960-07-12 | Geigy Ag J R | 7-triazinylamino-3-phenyl coumarins |
US3892807A (en) * | 1972-12-18 | 1975-07-01 | Hoechst Ag | Aromatic azomethines |
US3931215A (en) * | 1973-01-26 | 1976-01-06 | Hoechst Aktiengesellschaft | Benzofuran derivatives |
US3974172A (en) * | 1973-02-09 | 1976-08-10 | Hoechst Aktiengesellschaft | Benzofuran derivatives |
US4001130A (en) * | 1973-01-12 | 1977-01-04 | Hoechst Aktiengesellschaft | Optical brighteners |
EP0609894A2 (fr) * | 1993-02-05 | 1994-08-10 | Canon Kabushiki Kaisha | Complexe marqué et méthode d'analyse utilisant le-même |
JPH08179467A (ja) * | 1994-12-26 | 1996-07-12 | Konica Corp | ハロゲン化銀写真感光材料およびその現像処理方法 |
EP0747700A2 (fr) * | 1995-06-07 | 1996-12-11 | Carnegie-Mellon University | Complexe avec un grand décalage de stokes pour marquage fluorescent formé par couplage de cyanine et autres fluorochromes capables de transfert d'énergie résonance |
US5627027A (en) * | 1986-04-18 | 1997-05-06 | Carnegie Mellon University | Cyanine dyes as labeling reagents for detection of biological and other materials by luminescence methods |
WO2000053678A1 (fr) * | 1999-03-11 | 2000-09-14 | Dyomics | Colorants marqueurs proches de l'infrarouge (nir) compatibles aux lasers |
DE19937024A1 (de) * | 1999-08-05 | 2001-02-08 | Bayer Ag | Verwendung von Acylsulfonamido substituierten Polymethin-Farbstoffen als Fluoreszenz-Farbstoffe und/oder Marker |
EP1219626A1 (fr) * | 1999-09-20 | 2002-07-03 | Fuji Photo Film Co., Ltd. | Composes destines au marquage par fluorescence |
EP1318177A2 (fr) * | 2001-12-05 | 2003-06-11 | Dyomics GmbH | Composé, en particulier colorant marqueur, à base de polyméthines |
US20030135058A1 (en) * | 2000-04-12 | 2003-07-17 | Knut Reiner | Flurescent marker |
WO2004063749A1 (fr) * | 2003-01-08 | 2004-07-29 | Pharmacia & Upjohn Company Llc | Procede permettant de determiner des affinites moleculaires avec la serum-albumine humaine |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4886744A (en) | 1985-04-25 | 1989-12-12 | Polaroid Corporation | Fluorescent conjugates and biological diagnostic assay system |
JP3428715B2 (ja) | 1994-02-23 | 2003-07-22 | 東洋合成工業株式会社 | 感光性樹脂組成物 |
TW455616B (en) | 1997-11-03 | 2001-09-21 | Ciba Sc Holding Ag | New quinolinium dyes and borates, combinations thereof as photoinitiator compositions and photopolymerizable compositions comprising these photoinitiators |
-
2003
- 2003-11-28 DE DE10356130A patent/DE10356130A1/de not_active Withdrawn
-
2004
- 2004-11-26 AT AT04028161T patent/ATE513015T1/de active
- 2004-11-26 EP EP04028161A patent/EP1535969B1/fr active Active
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945033A (en) * | 1957-05-29 | 1960-07-12 | Geigy Ag J R | 7-triazinylamino-3-phenyl coumarins |
US3892807A (en) * | 1972-12-18 | 1975-07-01 | Hoechst Ag | Aromatic azomethines |
US4001130A (en) * | 1973-01-12 | 1977-01-04 | Hoechst Aktiengesellschaft | Optical brighteners |
US3931215A (en) * | 1973-01-26 | 1976-01-06 | Hoechst Aktiengesellschaft | Benzofuran derivatives |
US3974172A (en) * | 1973-02-09 | 1976-08-10 | Hoechst Aktiengesellschaft | Benzofuran derivatives |
US5627027A (en) * | 1986-04-18 | 1997-05-06 | Carnegie Mellon University | Cyanine dyes as labeling reagents for detection of biological and other materials by luminescence methods |
EP0609894A2 (fr) * | 1993-02-05 | 1994-08-10 | Canon Kabushiki Kaisha | Complexe marqué et méthode d'analyse utilisant le-même |
JPH08179467A (ja) * | 1994-12-26 | 1996-07-12 | Konica Corp | ハロゲン化銀写真感光材料およびその現像処理方法 |
EP0747700A2 (fr) * | 1995-06-07 | 1996-12-11 | Carnegie-Mellon University | Complexe avec un grand décalage de stokes pour marquage fluorescent formé par couplage de cyanine et autres fluorochromes capables de transfert d'énergie résonance |
WO2000053678A1 (fr) * | 1999-03-11 | 2000-09-14 | Dyomics | Colorants marqueurs proches de l'infrarouge (nir) compatibles aux lasers |
DE19937024A1 (de) * | 1999-08-05 | 2001-02-08 | Bayer Ag | Verwendung von Acylsulfonamido substituierten Polymethin-Farbstoffen als Fluoreszenz-Farbstoffe und/oder Marker |
EP1219626A1 (fr) * | 1999-09-20 | 2002-07-03 | Fuji Photo Film Co., Ltd. | Composes destines au marquage par fluorescence |
US20030135058A1 (en) * | 2000-04-12 | 2003-07-17 | Knut Reiner | Flurescent marker |
EP1318177A2 (fr) * | 2001-12-05 | 2003-06-11 | Dyomics GmbH | Composé, en particulier colorant marqueur, à base de polyméthines |
WO2004063749A1 (fr) * | 2003-01-08 | 2004-07-29 | Pharmacia & Upjohn Company Llc | Procede permettant de determiner des affinites moleculaires avec la serum-albumine humaine |
Non-Patent Citations (5)
Title |
---|
B.WETZL ET AL.: "Set of fluorochromophores in the wavelength range from 450 to 700 nm and suitable for labeling proteins and amino-modified DNA", J.CHROMATOGR..B, vol. 793, 2003, pages 83 - 92, XP004438970 * |
C.Y.CHEN ET AL.: "The absorption and the emission spectra of some substituted 3-Phenylcoumarins", HETEROCYCLES, vol. 7, no. 2, 1977, pages 933 - 945, XP009045844 * |
M.S.SCHIEDEL ET AL.: "Single-Compound Libraries of Organic Materials: Parellel Synthesis and Screening of Fluorescent Dyes", ANGEW.CHEM.INT.ED., vol. 40, no. 24, 2001, pages 4677 - 4680, XP002323070 * |
N.FOKIALAKIS ET AL.: "Estrogenic Activity of Phenylpropanoids from Sarcomelicope Megistophylla and structure determination of a new norneolignan", PLANTA MED, vol. 69, 2003, pages 565 - 568, XP009045848 * |
P.CZERNEY: "Heterocyclisch substituierte Cumarine aus beta-Chloropropen- iminiumsalzen", J.PRAKT.CHEM., vol. 324, no. 2, 1982, pages 255 - 266, XP002323071 * |
Also Published As
Publication number | Publication date |
---|---|
EP1535969B1 (fr) | 2011-06-15 |
DE10356130A1 (de) | 2005-06-23 |
EP1535969A2 (fr) | 2005-06-01 |
ATE513015T1 (de) | 2011-07-15 |
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